Reader Question #42: I must chill. How do I chill?

First I would like to say hello! And also, thank for you being so awesome and wise. And special thanks to Feministe for introducing me to your site a few weeks ago.

This morning I was writing an email to a friend about some dating angst I’m having and I found myself wondering “What would Captain Awkward have to say about this?” and figured I’d ask. So, Captain Awkward, what do I do about my dating angst? I’m not worried about getting the dates, exactly. I’ve joined an online dating site and it’s not my first time at this particular rodeo so I sort of know the ropes. I guess the problem I have is more…once I have the date. How do I avoid overthinking things? Getting too wrapped up in people too quickly? The last two times I tried dating I wound up in relationships with the first guy I met IRL (granted, the second relationship was pretty great and lasted three years so I clearly wasn’t doing everything wrong). Obviously, I told myself, I need to get better at DATING. I need to learn to be pickier (or less pickier?) and more casual, meet with more men before settling down.

Then, very recently, I went on my first date in over 3 and a half years. (I dated my most recent ex for 3 years, we were in love, it was wonderful, I thought he was “the one” and then he fell out of love and broke up with me 8 months ago, in case you were wondering why the recent dating gap.) Miracle of miracles – the gentleman was even cuter in person, charming, sweet, intelligent, funny. We hit it off fantastically, and ended the night promising that we would definitely have to get together again, though we didn’t make any concrete plans. He texted me a couple days later just to say hi, I texted him today regarding some story he’d told me on the date. . . but no 2nd date yet. It hasn’t even been a week yet, so this is no big deal, right? And yet. . . I am starting to get Crazy Brain. Crazy Brain is not being helped by all the annoying and sometimes conflicting and definitely unsolicited advice I’m getting from well-meaning friends: Women and men should be equal and shouldn’t play games, but don’t call, text, email him, let him always initiate. Don’t be afraid to ask him out but don’t make plans for Date #2 as I’d been the one to suggest we meet in person the first time (though he did initiate contact with me first, for whatever that’s worth) and now it’s his “turn”. Take things slow (Um…too late for this. When I said we hit it off, I meant we REALLY hit it off. If you get my drift.). Date other people, but don’t get too “loosey-goosey” (I’m actually not entirely sure what this means). Meanwhile, my gut is telling me to just go for it. If I know what I want, why not try and get it? (Even if that “it” is just a 2nd date.)

I guess my question for you is: How do I decide what to do, who to listen to? How do I know what is best for me to do, in this situation or in the future? How can I get my brain[loins] to step away from the ledge and chill the fuck out already? To be honest, I suppose I’m also looking for someone to tell me, for once, that what I’m doing or what I want to do is RIGHT, so long as it feels right to me. But I know I have a problem of letting my brain[heart/loins] get way ahead of things and I know that’s not really a good thing.

Thank you for any pearls of wisdom you can throw my way. I’m going to go back and reread everything you’ve tagged “dating” to see if that won’t help a little.

-Serial Monogamist

Dear Serial Monogamist:

Thanks for the nice words! As for your question, maybe we’re exactly the same? I’m sorry, I have no idea how to take it slow with dating. Intern Paul and I turned a one night stand into an almost 5 year stand (I think? Intern Paul, can I get a fact-check?) The major boyfriend before that? Same deal. There were plenty of times that didn’t happen, or I tried to turn what should have been a short-term thing into a long-term thing, but I guess I’m in the camp of “When it’s right, it’s easy, and things just fall into place, and you don’t have to worry about who asked who out last.”

Two very practical suggestions:

I would resist, at this stage, getting all up in each other’s Social Media. It’s too easy to obsess, and the more potential points of contact you have the more tempted you are to use all of them at once (or feel ignored via all of them at once).

Tell your loins to chill out. People have lives and when they meet someone great it sometimes takes some rearranging to have enough time to really incorporate a new dating partner. If you go a week or two without a date, that is normal and okay. It means he is a person with a life and he had plans, and you want someone to have a life. If you go two weeks without any contact at all, not even a quick text, THEN you are allowed to feel crazy, okay?

Maybe this will help. Right before I met Intern Paul, I went out with a depressed guy who didn’t have a phone. (He gave great massages. I was weak). After a lot of weird angst and communication annoyances (he was impossible to get a hold of), he dumped me because he was “too depressed to have a girlfriend right now.” And I was like, UGH, WHY DID I WASTE MY TIME TRYING TO MAKE IT WORK WITH THIS GUY? So I made a vow that I would not date anyone who was not as cool as my friends. Like, the actual time spent with the person had to be as fun as an evening out with my friends. And look, my friends are hilarious, and brilliant, and cool, and kind, and very quick (new people who come to our parties can either Keep Up or they leave, never to be seen again) and being around them is kind of effortless and great. And that’s what I want in a dude – someone who can keep up, who is kind, and who being around is effortless and great. Maybe that’s what you want in a dude, too? I’m not saying I never felt crazy again once I made that rule, but I felt crazy over a much higher caliber man.

Once you apply that test to a dating partner, a whole bunch of bullshit falls away, because friendship is based on reciprocity and enjoyment. So if you feel like calling or asking, call and ask. If you enjoy yourself, keep enjoying yourself. Dating relationships without reciprocity are no fun. Friendships without reciprocity are no fun either. I had to give an African Violet to a very cool person at the beginning of the year. She was putting a lot of kind effort into being my friend, and I wasn’t putting the same effort into her, and it felt weird, because it lacked reciprocity. So the questions in dating are, “Am I enjoying myself right now, in this moment?” and “If I take a step towards him, does he take one towards me or does he retreat?”

Can we go out again now? Howabout now? Maybe now? Would now be good?

Look, I hate The Rules and He’s Just Not That Into You and Men Are From Mars, Women Are From Venus and every single dating advice column in every single goddamn glossy woman’s magazine. Just fucking ignore it all. Be a person, go about your life, stop worrying if people like you (you can’t control that), so evaluate if you like them and are having a good time. And if you catch yourself feeling crazy, then go back to 1)Is he as awesome as my friends? 2) If I take a step towards him does he take a step towards me, or do I feel like I’m chasing?

And if you feel like you are chasing, stop chasing. Not because of stupid evo-psych bullshit about how men and women are supposed to behave, but because you need to do a reality check for reciprocity. If you don’t take any steps forward, does he take one towards you? I have a feeling that the right dude for you will be happy about your enthusiastic and straightforward ways, and someone who gets spooked because a lady asked him out wasn’t feeling it anyway. Other than that, I have no advice on playing it cool, because I am the Golden Retriever of Love, and when I like you I just say “Hey, you are awesome and I like you. Want to go to Hot Doug’s with me sometime?”

This is awesome, and also? Apparently I am also the Golden Retriever of Love.

k said: May 2, 20118:20 am

Oh girl, I too am apparently you! Same issues with overthinking things, same experience that if a relationship is “right” it doesn’t really matter who calls whom or what you ordered on the first date or etc.

I’d like to give one piece of loins-directed advice to Ms. Serial Monogamist, if y’all don’t mind:

If you don’t have an awesome vibrator, shell out some cash for an awesome vibrator. If you don’t already know how to find porn you enjoy (whether written, or still photos, or videos) start doing some xxx-rated research.

What I’m saying here, is make sure that you getting off is not contingent upon some dude or other being in the room. Depending upon how much you masturbate, fully 2/3 of your Crazy Brain may actually be due to sexual frustration. I know solo sex ain’t the same, but it will help.

I’ll have the Apricot and Brandy Chicken Sausage with Passion Fruit Mustard and Brie-Blue Cheese, please.

Sid said: May 2, 20117:37 pm

Sage advice as always, Captain.

Speaking of Hot Doug’s, Summer Hours are taking effect for me next Monday. Perhaps there could be celebratory sausage.

JenniferP said: May 3, 20112:42 am

I have to be down at school by 12:45, but a when-they-open excursion: Delight!

J-Dub said: May 2, 201110:08 pm

Thanks for answering my question, Captain! When I saw that you’d posted this I actually squealed out loud, just a little. And then when I actually read it, I breathed a sigh of relief because a) apparently I’m not crazy and not the only person who acts/thinks this way (And thank you commentors for further confirming this! We are a great big band of Golden Retrievers.)and b) your advice makes sense and has already been totally helpful! I feel confident that I’m doing things the right way (where “right” = what my instinct is telling me to do) but I do feel like I’m now better able to take a step back and look at things more clearly.
So, an update on the situation, in case you’re all curious: almost immediately after I emailed you, the Man in Question contacted me to ask if I’d be interested in joining him for a movie playing that night at a local film festival. I was interested, and we went, and had a great time, and when he dropped me off said it was now my turn to plan a good date for us. We had date 3 on Saturday and it was fantastic and loads of fun, and I will definitely be seeing him again. It’s early days yet, so we haven’t had any sort of “exclusivity” talk but in all honesty, that’s fine. It feels good, I’m enjoying myself, he is most certainly as awesome as my friends are, and however it turns out in the end is OK. Coincidentally, I’ve noticed a sudden drop off in the number of attractive (to me), interesting, “fit most of my criteria” dudes on the Online Dating Site. (And those few I’ve seen that I’d be willing to talk with/meet haven’t responded to me, which is really fine. I mean, it goes both ways and not everyone is going to be interested in everyone and the fact that being rejected/ignored doesn’t bother me one jot says a good deal about my improved mental health/self confidence, so there’s that.)
Thank you for helping me chill, Captain! Your efforts have already born some fruit and I’m happy to know I can refer back to this post in the future when I’m feeling less self-assured/more crazy.

JenniferP said: May 3, 20112:42 am

Glad it’s going well!

J-Dub said: May 4, 20118:34 pm

So, to further update my update, I’ve only spoken (a text exchange, actually, and I know some of you are going to be all “aieee just make phone calls or email him already” but 1) I actually hate talking on the phone and 2) I don’t have his off-Dating Site email and I really like the immediacy and casualness of the text) to Dude once, this morning, no further date plans yet…and I know this is totally normal. I know! CrazyBrain keeps trying to win and I am trying to beat it into submission. I printed out your answer and highlighted certain crucial points and have re-read those points an embarassing number of times in the last few days, figuring eventually it will stick and I’ll truly believe what I’m telling myself. :)
My task for this afternoon is to make a list of everything I’m worried about in re. dating in general and this person in particular and then write rebuttals to those worries.

J-Dub said: May 4, 20118:43 pm

And this is only related to this post because of the African Violet reference, but I was reading one of those “What to get your mom for Mother’s Day” lists somewhere online and they suggested an African Violet as a good gift for Mom. This made me really sad because I now think of those flowers as the “Its time to end this relationship” emblem.

And our parties are where you take new boyfriends to see if they’ll stick.

FirstAidKit said: February 21, 20125:33 am

I know this is old but DAMN did I need to read this. I get a full, huge case of the Crazybrain that lasts approximately 2 weeks after sleeping with someone – usually quite a crucial stage of the interaction (taking it slow, I am bad at it). I am much better than I used to be but am still getting to grips with it.